反应详情

温度

100 °C

Cs2CO3 (1.16 g, 4.95 mmol) was added to a solution of methanesulfonic acid 1-benzhydryl-azetidin-3-yl ester (193a) (756 mg, 2.38 mmol) and 4-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (3e) (440 mg, 1.98 mmol) in DMF (6 mL). The mixture was heated to 100° C. for 4 hr, quenched with H2O (100 mL) and extracted with EtOAc (100 mL). The organic layer was washed with H2O, dried over MgSO4 and concentrated. The residue was purified by flash column chromatograph eluting with 30-40% EtOAc in hexanes to give a white sold (740 mg, 84% yield). 1H NMR (400 MHz, CDCl3) δ 7.44 (d, J=7.07 Hz, 4 H) 7.27-7.32 (m, 4 H) 7.18-7.25 (m, 2 H) 7.04 (d, J=1.01 Hz, 1 H) 6.81 (d, J=1.01 Hz, 1 H) 4.87 (t, J=5.81 Hz, 1 H) 3.85 (s, 3 H) 3.76 (ddd, J=7.52, 5.87, 2.02 Hz, 2 H) 3.12 (ddd, J=7.33, 5.56, 1.77 Hz, 2 H) 2.99 (s, 2 H) 1.49 (s, 6 H); LCMS for C28H29NO4 m/z 444.20 (M+H)+.

1. customquenched with H2O (100 mL)
2. extractionextracted with EtOAc (100 mL)
3. washThe organic layer was washed with H2O
4. dry with materialdried over MgSO4
5. concentrationconcentrated
6. customThe residue was purified by flash column chromatograph
7. washeluting with 30-40% EtOAc in hexanes
8. customto give